1) Doubt it, it's listed as a "misc" item. I figured it had to do with *that* doctor, but it seems odd to get it so soon while it has use muuuuuuch later. After it did nothing I reloaded so I still got it for using there though.
2) Eh, I just dismissed my lockpicking henchmen

.
3) Well, I murdered him on the Vengeance, so guess that's that.
5) Yeah, it's kinda odd, it's the only "reward" that was actually rather good, took vendors some time to catch up to it's value. And yeah, all the other options closed it, this one didn't so I figured there was more to it, like the original owner claiming it. Guess not.
6)

.
Thanks for the answers all. Guess it's off to Nameless Isle.